L-Lactic acid (YMDB00247)

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Identification

YMDB ID

YMDB00247

Name

L-Lactic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

D-Lactic acid, also known as D-lactate or D-milchsaeure, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. D-Lactic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Lactic acid exists in all living species, ranging from bacteria to humans. D-Lactic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(+)-Lactate
(+)-Lactic acid
(alpha)-Lactate
(alpha)-Lactic acid
(S)-(+)-2-Hydroxypropanoate
(S)-(+)-2-Hydroxypropanoic acid
(S)-(+)-Lactic acid
(S)-2-hydroxy-Propanoate
(S)-2-hydroxy-Propanoic acid
(S)-2-Hydroxypropanoate
(S)-2-Hydroxypropanoic acid
(S)-2-Hydroxypropionate
(S)-2-Hydroxypropionic acid
(S)-Lactate
(S)-Lactic acid
1-Hydroxyethane 1-carboxylate
1-Hydroxyethane 1-carboxylic acid
1-Hydroxyethanecarboxylate
1-Hydroxyethanecarboxylic acid
2-Hydroxypropanoate
2-Hydroxypropanoic acid
2-Hydroxypropionate
a-Hydroxypropanoate
a-Hydroxypropanoic acid
a-Hydroxypropionate
a-Hydroxypropionic acid
alpha-Hydroxypropanoate
alpha-Hydroxypropanoic acid
alpha-Hydroxypropionate
alpha-Hydroxypropionic acid
d-Lactic acid
Espiritin
hydroxypropionic acid
l-(+)- lactic acid
L-(+)-Lactic acid
L-2-Hydroxypropanoate
L-2-Hydroxypropanoic acid
L-Lactate
l-lactic acid
Lactate
Lactic acid
Lactic acid, L-
Milk acid
Paralactic acid
Propanoic acid, 2-hydroxy-, (S)-
Propel
Sarcolactic acid
Tisulac
(-)-Lactic acid
(R)-(-)-Lactic acid
D-2-Hydroxypropanoic acid
D-2-Hydroxypropionic acid
D-Milchsaeure
D-Lactate
(-)-Lactate
(R)-(-)-Lactate
D-2-Hydroxypropanoate
D-2-Hydroxypropionate
(R)-2-Hydroxypropanoate
(R)-2-Hydroxypropanoic acid
(R)-2-Hydroxypropionate
(R)-2-Hydroxypropionic acid
(R)-a-Hydroxypropionate
(R)-a-Hydroxypropionic acid
(R)-alpha-Hydroxypropionate
(R)-alpha-Hydroxypropionic acid
(R)-Lactate
(R)-Lactic acid
D-(-)-Lactate
D-(-)-Lactic acid
delta-(-)-Lactate
delta-(-)-Lactic acid
delta-2-Hydroxypropanoate
delta-2-Hydroxypropanoic acid
delta-2-Hydroxypropionate
delta-2-Hydroxypropionic acid
delta-Lactate
delta-Lactic acid
DLA
L-(+)-Lactate
2 Hydroxypropanoic acid
2 Hydroxypropionic acid
Ammonium lactate
L Lactic acid
2-Hydroxypropionic acid
D Lactic acid
Lactate, ammonium

CAS number

79-33-4

Weight

Average: 90.0779
Monoisotopic: 90.031694058

InChI Key

JVTAAEKCZFNVCJ-REOHCLBHSA-N

InChI

InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1

IUPAC Name

(2R)-2-hydroxypropanoic acid

Traditional IUPAC Name

D-lactic acid

Chemical Formula

C₃H₆O₃

SMILES

[H]OC(=O)[C@@]([H])(O[H])C([H])([H])[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Alpha hydroxy acids and derivatives

Direct Parent

Alpha hydroxy acids and derivatives

Alternative Parents

Substituents

Alpha-hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-hydroxypropanoic acid (CHEBI:42111 )

Physical Properties

State

Liquid

Charge

Melting point

16.8 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	562 g/L	ALOGPS
logP	-0.79	ALOGPS
logP	-0.47	ChemAxon
logS	0.79	ALOGPS
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	18.84 m³·mol⁻¹	ChemAxon
Polarizability	8.05 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular
mitochondrion
cytoplasm

Organoleptic Properties

Flavour/Odour	Source
Acidic	FDB030146
Odorless	FDB030146

SMPDB Pathways

Pyruvate metabolism

PW002447

KEGG Pathways

Glycolysis / Gluconeogenesis	ec00010
Propanoate metabolism	ec00640
Pyruvate metabolism	ec00620

SMPDB Reactions

L-Lactic acid + NAD ↔ Pyruvic acid + NADH + hydron

L-Lactic acid + ferricytochrome c Pyruvic acid + Ferrocytochrome + hydron

KEGG Reactions

L-Lactic acid + ferricytochrome c → ferrocytochrome c + Pyruvic acid

NAD + water + Lactaldehyde → NADH + L-Lactic acid + hydron

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
533 ± 44 µM	hops, malted barley	anaerobic	Baker's yeast	PMID: 16448171
Conversion Details Here

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00kb-0900000000-fb59ec16914501aa19ab	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014j-0900000000-c4d9e12b4b0150eda54b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-0900000000-fb59ec16914501aa19ab	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-a3691f383d440fb00e1f	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-9620000000-f7faa7db9c1be3d9d975	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-9000000000-704f8ff33156c82a02d1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000m-9000000000-023931446d9bb3330e7f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-000l-9000000000-0fb29afb128baea2240b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-000i-9000000000-d7cd347946e49a57860e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-aee01e43e8ee93db755d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000f-9000000000-581a00222505e9e4b458	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-5bfd9fdf1c0df2054452	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-9000000000-5f417f4a6d08f0ab00ed	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dm-9000000000-df7a94bb1a9cf6e78e1a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-9000000000-dc2a1b965287b9dfee9c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-c3686a681cc9bbf039e1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-ddad20647c2ac56efd22	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-b728b45617afcc6b67da	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-b586cb8f053eb4465b4e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-400a5f1c0dfcc32ef2bb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-9000000000-ad5eb77c7e0a96f3a40a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-00ba25458eb6c0cc2940	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-00ba25458eb6c0cc2940	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-00ba25458eb6c0cc2940	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-002b-9000000000-50213d6b39ef9741c466	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Almeida, C., Duarte, I. F., Barros, A., Rodrigues, J., Spraul, M., Gil, A. M. (2006). "Composition of beer by 1H NMR spectroscopy: effects of brewing site and date of production." J Agric Food Chem 54:700-706.16448171
Inoue, Y., Watanabe, K., Shimosaka, M., Saikusa, T., Fukuda, Y., Murata, K., Kimura, A. (1985). "Metabolism of 2-oxoaldehydes in yeasts. Purification and characterization of lactaldehyde dehydrogenase from Saccharomyces cerevisiae." Eur J Biochem 153:243-247.3908097
Casal, M., Paiva, S., Andrade, R. P., Gancedo, C., Leao, C. (1999). "The lactate-proton symport of Saccharomyces cerevisiae is encoded by JEN1." J Bacteriol 181:2620-2623.10198029
Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666

Synthesis Reference:

Lao, Hanzhang; Sun, Jianrong; Wang, Jian; Qian, Zhiliang. Process for preparation of high-purity L-lactic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 9pp.

External Links:

Resource	Link
CHEBI ID	422
HMDB ID	HMDB00190
Pubchem Compound ID	107689
Kegg ID	C00186
ChemSpider ID	96860
FOODB ID	FDB030146
Wikipedia	Lactic_acid
BioCyc ID	L-LACTATE

Enzymes

Protein Details

1. Cytochrome b2, mitochondrial

General function:: Involved in catalytic activity
Specific function:: (S)-lactate + 2 ferricytochrome c = pyruvate + 2 ferrocytochrome c + 2 H(+)
Gene Name:: CYB2
Uniprot ID:: P00175
Molecular weight:: 65538.79688

Reactions

(S)-lactate + 2 ferricytochrome c → pyruvate + 2 ferrocytochrome c + 2 H(+).

Protein Details

2. Cytochrome c iso-1

General function:: Involved in iron ion binding
Specific function:: Electron carrier protein. The oxidized form of the cytochrome c heme group can accept an electron from the heme group of the cytochrome c1 subunit of cytochrome reductase. Cytochrome c then transfers this electron to the cytochrome oxidase complex, the final protein carrier in the mitochondrial electron-transport chain
Gene Name:: CYC1
Uniprot ID:: P00044
Molecular weight:: 12181.90039

Reactions

Protein Details

3. Cytochrome c iso-2

General function:: Involved in iron ion binding
Specific function:: Electron carrier protein. The oxidized form of the cytochrome c heme group can accept an electron from the heme group of the cytochrome c1 subunit of cytochrome reductase. Cytochrome c then transfers this electron to the cytochrome oxidase complex, the final protein carrier in the mitochondrial electron-transport chain
Gene Name:: CYC7
Uniprot ID:: P00045
Molecular weight:: 12532.2998

Reactions

Transporters

Protein Details

1. Carboxylic acid transporter protein homolog

General function:: Involved in carbohydrate transmembrane transporter activity
Specific function:: Essential to lactate transport
Gene Name:: JEN1
Uniprot ID:: P36035
Molecular weight:: 69375.60156

Structure for #<Compound:0xa7651844>

Enzymes

Reactions

Reactions

Reactions

Transporters